I really like sex and the city. It's still very relavent today, and the cast reminds me of some of my catty friends that I have had in the past. I think the point of the show is that the main cast are not likable and create problems for themselves.
As for books, I really think that users here would enjoy confessions of a mask by mishima, as well as the plague by camus.
I haven't watched anime in a while, but I really liked death note and fullmetal alchemist brotherhood. If you have any recommendations, I would happily look at them.